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药品详细

Cimetidine(西咪替丁)

化学结构式图
中文名
西咪替丁
英文名
Cimetidine
分子式
C10H16N6S
化学名
(Z)-1-cyano-2-methyl-3-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine
分子量
Average: 252.339
Monoisotopic: 252.115715232
CAS号
51481-61-9
ATC分类
A02B 未知
药物类型
small molecule
阶段
approved
商品名
Acibilin;Acinil;Cimal;Cimetag;Cimetum;Dyspamet;Edalene;Eureceptor;Gastromet;Peptol;Tagamet;Tagamet HB;Tagamet HB 200;Tametin;Tratul;Ulcedin;Ulcedine;Ulcerfen;Ulcimet;Ulcofalk;Ulcomedina;Ulcomet;Ulhys;
同义名
Cimetidine A/AB;Cimetidine Hcl;
基本介绍

A histamine congener, it competitively inhibits histamine binding to histamine H2 receptors. Cimetidine has a range of pharmacological actions. It inhibits gastric acid secretion, as well as pepsin and gastrins output. It also blocks the activity of cytochrome P-450 which might explain proposals for use in neoadjuvant therapy. [PubChem]

生产厂家
  • Actavis mid atlantic llc
  • Apotex inc
  • Contract pharmacal corp
  • Dava pharmaceuticals inc
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Endo pharmaceuticals inc
  • Glaxosmithkline
  • Hi tech pharmacal co inc
  • Hospira inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • L perrigo co
  • Lek pharmaceuticals d d
  • Luitpold pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Novex pharma
  • Perrigo co
  • Pharmaceutical assoc inc div beach products
  • Pliva inc
  • Roxane laboratories inc
  • Sandoz inc
  • Teva parenteral medicines inc
  • Teva pharmaceuticals usa
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Wockhardt eu operations (swiss) ag
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Michnovicz JJ, Galbraith RA: Cimetidine inhibits catechol estrogen metabolism in women. Metabolism. 1991 Feb;40(2):170-4. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Imidazoles
Substructures
  • Ethers
  • Nitriles and Derivatives
  • Cyanides
  • Imidazoles
  • Heterocyclic compounds
  • Guanidines
  • Aromatic compounds
  • Carboxamidines
  • Imines
  • Cyanamides
适应症
gastric acid RELATED DISORDERS 中和胃酸;
药理
Indication For the treatment and the management of acid-reflux disorders (GERD), peptic ulcer disease, heartburn, and acid indigestion.
Pharmacodynamics Cimetidine is a histamine H2-receptor antagonist. It reduces basal and nocturnal gastric acid secretion and a reduction in gastric volume, acidity, and amount of gastric acid released in response to stimuli including food, caffeine, insulin, betazole, or pentagastrin. It is used to treat gastrointestinal disorders such as gastric or duodenal ulcer, gastroesophageal reflux disease, and pathological hypersecretory conditions. Cimetidine inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Other actions of Cimetidine include an increase in gastric bacterial flora such as nitrate-reducing organisms.
Mechanism of action Cimetidine binds to an H2-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity.
Absorption Rapid 60-70%
Volume of distribution Not Available
Protein binding 15-20%
Metabolism
Hepatic
Route of elimination The principal route of excretion of cimetidine is the urine.
Half life 2 hours
Clearance Not Available
Toxicity Symptoms of overdose include nausea, vomiting, diarrhea, increased saliva production, difficulty breathing, and a fast heartbeat.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00232 Cimetidine Pathway SMP00232
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 142 °C PhysProp
water solubility 9380 mg/L (at 25 °C) MCFARLAND,JW ET AL. (2001)
logP 0.40 HANSCH,C ET AL. (1995)
logS -1.35 ADME Research, USCD
Caco2 permeability -5.89 ADME Research, USCD
pKa 6.8 TOMLINSON,E & HAFKENSCHEID,TL (1986)
Predicted Properties
Property Value Source
water solubility 8.16e-01 g/l ALOGPS
logP 0.44 ALOGPS
logP -0.11 ChemAxon
logS -2.5 ALOGPS
pKa (strongest acidic) 13.38 ChemAxon
pKa (strongest basic) 6.91 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 88.89 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 70.32 ChemAxon
polarizability 27.47 ChemAxon
药物相互作用
Drug Interaction
Acenocoumarol Cimetidine may increase the anticoagulant effect of acenocoumarol.
Alfentanil Increases the effect of the narcotic
Alprazolam Cimetidine may increase the effect of the benzodiazepine, alprazolam.
Aminophylline Cimetidine may increase the serum concentration of aminophylline by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of aminophylline if cimetidine is initiated, discontinued or dose changed.
Amitriptyline Cimetidine may increase the effect of the tricyclic antidepressant, amitriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amitriptyline if cimetidine is initiated, discontinued or dose changed.
Amoxapine Cimetidine may increase the effect of the tricyclic antidepressant, amoxapine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of amoxapine if cimetidine is initiated, discontinued or dose changed.
Anisindione Cimetidine may increase the anticoagulant effect of anisindione.
Astemizole Increased risk of cardiotoxicity and arrhythmias
Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
Bendamustine CA1A2 hepatic enzyme metabolism is affected by increased amounts of bendamustine by cimetidine. In addition, decreased conversion of bendamustine to active metabolites occurs. Amounts of active metabolites may be decreased. Decreased conversion of bendamustine to active metabolites also occurs.
Bromazepam Co-administration with cimetidine will cause a reduction in bromazepam clearance and increases half-life.
Carbamazepine Cimetidine may increase the serum concentration of carbamazepine during the first few days of concomitant therapy. Monitor for changes in the therapeutic and adverse effects of carbamazepine if cimetidine is initiated, discontinued or dose changed.
Carmustine Increases myelosuppression caused by carmustine
Cefditoren H2-Antagonists such as cimetidine may decrease the serum concentration of cefditoren. Cefditoren prescribing information recommends to avoid concomitant use with H2-antagonists (eg, famotidine, ranitidine) and antacids as well. Consider alternative methods to minimize/control acid reflux (eg, diet modification) or alternative antimicrobial therapy if use of H2-antagonists can not be avoided.
Chlordiazepoxide Cimetidine may increase the effect of the benzodiazepine, chlordiazepoxide.
Clomipramine Cimetidine may increase the effect of the tricyclic antidepressant, clomipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of clomipramine if cimetidine is initiated, discontinued or dose changed.
Clonazepam Cimetidine may increase the effect of the benzodiazepine, clonazepam.
Clorazepate Cimetidine may increase the effect of the benzodiazepine, clorazepate.
Clozapine Cimetidine may increase the serum concentratin of clozapine. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of clozapine if cimetidine is initiated, discontinued or dose changed.
Codeine Cimetidine may decrease the therapeutic effect of codeine by decreasing its metabolism to its active metabolite, morphine. Monitor for changes in the therapeutic effect of codeine if cimetidine is initiated, discontinued or dose changed.
Desipramine Cimetidine may increase the effect of the tricyclic antidepressant, desipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of desipramine if cimetidine is initiated, discontinued or dose changed.
Diazepam Cimetidine may increase the effect of the benzodiazepine, diazepam.
Dicumarol Cimetidine may increase the anticoagulant effect of dicumarol.
Dihydroquinidine barbiturate Increases the effect of quinidine
Dofetilide Increases effect/toxicity of dofetilide
Donepezil Possible antagonism of action
Doxepin Cimetidine may increase the effect of the tricyclic antidepressant, doxepin, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of doxepin if cimetidine is initiated, discontinued or dose changed.
Dyphylline Increases the effect of theophylline
Eltrombopag Affects hepatic CYP1A2 metabolism, will decrease effect/level of eltrombopag. Affects hepatic CYP2C9/10 metabolism, will decrease effect/level of eltrombopag.
Enoxacin Cimetidine may decrease the absorption of enoxacin.
Epirubicin Cimetidine can increase epirubicin levels
Estazolam Cimetidine may increase the effect of the benzodiazepine, estazolam.
Ethotoin Increases the effect of hydantoin
Fentanyl Cimetidine, a moderate CYP3A4 inhibitor, may decrease the metabolism of fentanyl. Closely monitor changes in the therapeutic and adverse effects of fentanyl if cimetidine is initiated, discontinued or dose changed.
Flecainide Cimetidine, a moderate CYP2D6 inhibitor, may decrease the metabolism of flecainide.
Flurazepam Cimetidine may increase the effect of the benzodiazepine, flurazepam.
Fosphenytoin Cimetidine may increase the serum concentration of fosphenytoin by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of fosphenytoin if cimetidine is initiated, discontinued or dose changed.
Galantamine Possible antagonism of action
Halazepam Cimetidine may increase the effect of the benzodiazepine, halazepam.
Heroin Cimetidine increases the effect of the narcotic
Imipramine Cimetidine may increase the effect of the tricyclic antidepressant, imipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of imipramine if cimetidine is initiated, discontinued or dose changed.
Itraconazole The H2-receptor antagonist, cimetidine, may decrease the absorption of itraconazole.
Ketazolam Cimetidine may increase the effect of the benzodiazepine, ketazolam.
Ketoconazole The H2-receptor antagonist, cimetidine, may decrease the absorption of ketoconazole.
Labetalol Cimetidine may increase the serum concentration of labetolol by decreasing its metabolism.
Lidocaine Increases the effect and toxicity of lidocaine
Mephenytoin Increases the effect of hydantoin
Metformin Cimetidine may increase the therapeutic and adverse effects of metformin by increasing its serum concentration. Consider alternate therapy.
Methadone Cimetidine, a moderate CYP3A4 inhibitor, may increase the serum concentration of metahdone, a CYP3A4 substrate. Monitor for changes in the therapeutic and adverse effects of methadone if cimetidine is initiatied, discontinued or dose changed.
Metoprolol Cimetidine may increase the serum concentration of metoprolol by decreasing its metabolism.
Midazolam Cimetidine may increase the effect of the benzodiazepine, midazolam.
Moclobemide Cimetidine may increase the serum concentration of moclobemide by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of moclobemide if cimetidine is initiated, discontinued or dose changed.
Nalbuphine Increases the effect of the narcotic
Nifedipine Cimetidine may increase the effect of the calcium channel blocker, nifedipine.
Nimodipine Cimetidine increases the effect of the calcium channel blocker, nimodipine.
Nitrendipine Cimetidine increases the effect of the calcium channel blocker, nitrendipine.
Nortriptyline Cimetidine may increase the effect of the tricyclic antidepressant, nortriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of nortriptyline if cimetidine is initiated, discontinued or dose changed.
Oxtriphylline Cimetidine may increase the serum concentration of oxtriphylline by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of oxtriphylline if cimetidine is initiated, discontinued or dose changed.
Oxycodone Cimetidine, a moderate CYP3A4 inhibitor, may decrease the metabolism of oxycodone. Monitor for changes in the therapeutic and adverse effects of oxycodone if cimetidine is initiated, discontinued or dose changed.
Oxymorphone Increases the effect of the narcotic
Pazopanib Affects CYP3A4 metabolism therefore will decrease levels or effect of pazopanib. Consider alternate therapy.
Phenytoin Cimetidine may increase the therapeutic effect of phenytoin.
Posaconazole Significant decrease of posaconazole levels
Pramipexole Cimetidine may increase the effect and toxicity of pramipexole.
Prazepam Cimetidine may increase the effect of the benzodiazepine, prazepam.
Procainamide The histamine H2-receptor antagonist, cimetidine, may increase the effect of procainamide.
Propoxyphene Cimetidine, a moderate CYP3A4 inhibitor, may decrease the metabolism of propoxyphene. Monitor for changes in the therapeutic and adverse effects of propoxyphene if cimetidine is intitiated, discontinued or dose changed.
Propranolol Cimetidine may increase the serum concentration of propranolol by decreasing its metabolism.
Protriptyline Cimetidine may increase the effect of tricyclic antidepressant, protriptyline, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of trimipramine if cimetidine is initiated, discontinued or dose changed.
Quazepam Cimetidine may increase the effect of the benzodiazepine, quazepam.
Quinidine Cimetidine may increase the serum concentration of quinidine. Monitor for changes in the therapeutic and adverse effects of quinidine if cimetidine is initiated, discontinued or dose changed.
Quinidine barbiturate Increases the effect of quinidine
Rivastigmine Possible antagonism of action
Roflumilast Increases roflumilast levels.
Sildenafil Increases the effect and toxicity of sildenafil
Sufentanil Increases the effect of the narcotic
Tacrine The metabolism of Tacrine, a CYP1A2 substrate, may be reduced by Cimetidine, a CYP1A2 inhibitors. Monitor the efficacy and toxicity of Tacrine if Cimetidine is initiated, discontinued or if the dose is changed.
Tacrolimus Cimetidine may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Cimetidine therapy is initiated, discontinued or altered.
Tamoxifen Cimetidine may decrease the therapeutic effect of Tamoxifen by decreasing the production of active metabolites. Consider alternate therapy.
Tamsulosin Cimetidine, a CYP3A4/2D6 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4/2D6 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Cimetidine is initiated, discontinued, or dose changed.
Terfenadine Increased risk of cardiotoxicity and arrhythmias
Theophylline Cimetidine may increase the effect of theophylline.
Ticlopidine Cimetidine may increase Ticlopidine levels. Avoid concomitant therapy.
Timolol Cimetidine may increase the serum concentration of timolol by decreasing its metabolism.
Tizanidine Cimetidine may decrease the metabolism and clearance of Tizanidine. Consider alternate therapy or use caution during co-administration.
Tolazoline Anticipated loss of efficacy of tolazoline
Tolterodine Cimetidine may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
Tramadol Cimetidine may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance. Cimetidine may decrease the effect of Tramadol by decreasing active metabolite production.
Trazodone The CYP3A4 inhibitor, Cimetidine, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Cimetidine is initiated, discontinued or dose changed.
Triazolam Cimetidine may increase the serum concentration of triazolam by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of triazolam if cimetidine is initiated, discontinued or dose changed.
Trimipramine Cimetidine may increase the effect of tricyclic antidepressant, trimipramine, by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of trimipramine if cimetidine is initiated, discontinued or dose changed.
Vilazodone Cimetidine may decrease the metabolism of Selective Serotonin Reuptake Inhibitors. Consider using an alternative H2-antagonist to avoid the risk of selective serotonin reuptake inhibitor (SSRI) toxicity. Monitor for increased therapeutic or toxic effects of SSRI if cimetidine is initiated/dose increased, or decreased effects if cimetidine is discontinued/dose decreased.
Warfarin Cimetidine may increase the serum concentration of warfarin. Monitor for changes in prothrombin time and therapeutic and adverse effects of warfarin if cimetidine is initiated, discontinued or dose changed.
Zaleplon Cimetidine may increase the serum concentration of zaleplon by decreasing its metabolism. Reduce the initial dose of zaleplon to 5 mg in patients receiving cimetidine.
食物相互作用
  • Avoid alcohol.
  • Best effect when taken with food.
  • Limit caffeine intake.

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